He enlisted in the Third Virginia regiment, in which he became a lieutenant, and subsequently took part in the battles of Harlem Heights, White Plains, Trenton (where he was wounded), Brandywine, Germantown, and Monmouth.

A skirmish, fought the next day, opposite the west front of the present Columbia University, and known as the affair of Harlem Heights, cost the British a loss of seventy of their light infantry.

Vanderbilt in 1866 became attorney for the New York & Harlem railway, in 1869 was appointed attorney of the newly consolidated New York Central & Hudson river railway, of which he soon became a director, and in 1875 was made general counsel for the entire Vanderbilt system of railways.

When we got to Jersey City at six o'clock Friday evening we were obliged to cross the Harlem River in a ferry-boat.

Washington prepared to withstand the British behind fortifications on Harlem Heights, but discovering that Howe was attempting to outflank him by landing troops in the rear he retreated to the mainland, leaving only a garrison at Fort Washington, and established a line of fortified camps on the hills overlooking the Bronx river as far as White Plains.